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Antinociceptive and Smooth Muscle Relaxant Activity of Croton Tiglium L Seed: an In-Vitro and In-Vivo Study

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Antinociceptive and Smooth Muscle Relaxant Activity of Croton Tiglium L Seed: an In-Vitro and In-Vivo Study Iranian Journal of Pharmaceutical Research (2012), 11 (2): 611-620 Copyright © 2012 by School of Pharmacy Received: December 2010 Shaheed Beheshti University of Medical Sciences and Health Services Accepted: August 2011 Original Article Antinociceptive and Smooth Muscle Relaxant Activity of Croton tiglium L Seed: An In-vitro and In-vivo Study Zhen Liua, Wenyuan Gaoa*, Jingze Zhanga and Jing Hua,b aSchool of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China. bSchool of Chinese Medicine, Tianjin University of TCM, Tianjin 300193, China. Abstract The seed of Croton tiglium L. (SCT) is a well known folk medicine. In China, it has used to treat gastrointestinal disorders, intestinal inflammation, rheumatism, and so on. Previous studies established its purgative and inflammation properties. In addition, the effects of essential oil of SCT on intestinal transit and gastrointestinal tract has been studied. In the present study, we evaluated the antinociceptive effect of SCT through the writhing test in mice, investigated the effects of it on spontaneous smooth muscle contractions of isolated rabbit jejunum and examined the in-vitro results through the in-vivo small intestine propulsion. We further investigated the possible compounds using HPLC-MS, and six compounds were tentatively identified as phorbol esters. Furthermore, the possible fragmentation pathways of phorbol esters were proposed, and we also detected the possible compounds in the active parts. Keywords: Croton tiglium L; Intestinal propulsion; Smooth muscle; Rabbit jejunum; Antinociceptive; Phorbol esters. Introduction guinea pig colonic smooth muscle cell has been studied, which regulates the gastrointestinal The genus Croton belongs to the family transit in mice, and affects the inflammatory and Euphorbiaceae. The seed of Croton tiglium L. immunological milieu (2, 5). In the previous (SCT) is well known as Ba-Dou in China. It has study, we reported the effect of croton oil on been used as a traditional medicine for many spontaneous smooth muscle contractions in applications such as constipation, a purgative, and isolated rabbit jejunum and the underlying treating dyspepsia and dysenteria. The Chinese mechanisms (6). From the leaves of C. tiglium, had written records in the second century B.C. a pyrazine derivative crotonine was isolated and for using it to treat the gastrointestinal disorders, showed significance analgesic effects (7). intestinal inflammation, rheumatism, headache, Some tigliane phorbol esters have been peptic ulcer and visceral pain (1-4). Croton oil, isolated from C. tiglium previously. Among the essential oil of SCT, as the effective part, Croton species, only C. tiglium has been has been reported to have purgative, analgesic, extensively studied as the source of phorbol antimicrobial, and inflammatory properties (1, derivatives (8, 9). Phorbol esters have been 3). Besides, the direct effect of Croton oil on shown to be responsible for eliciting a remarkable range of biochemical effects except * Corresponding author: tumor promoting (10, 11), such as skin irritant E-mail: [email protected] effects (12), platelet aggregation (13), and cell Liu Z et al. / IJPR (2012), 11 (2): 611-620 differentiation (14). Although the ability of these induced writhing in mice, and investigated the compounds to promote tumors presents the active fraction of SCT on spontaneous smooth potential limitation of their utility, it should be muscle contraction in isolated rabbit jejunum. stressed that there are many phorbol esters that By the results of the muscle contraction, we exert the profound beneficial biological effects tested the effect of SCT on intestinal propulsion without tumorigenesis. 12-O-tigloylphorbol-13- in mice using the charcoal method. The decanoate isolated from croton oil demonstrated effective compounds of SCT and the possible antileukemia activity against the P-388 leukemia fragmentation of phorbol esters are also in mice (15). Eight phorbol esters isolated from described in this assay. the C. tiglium have the ability to inhibit an HIV- induced cytopathic effect on MT-4 cells (16). Experimental The most investigated activity of the phorbol esters is their binding and activation of protein Plant materials and animals kinase C (PKC), which plays a critical role in The seed of C. tiglium was provided by Tianjin signal transduction pathway and regulates the Lerentang Pharmaceutical Factory (Tianjin, cell growth and differentiation (17, 18). PKC China) and identified by Professor Wenyuan isoforms are distributed in the small intestine Gao from School of Pharmaceutical Science and involved in modifying the functions of and Technology, Tianjin University, China. The intestinal muscle including the generation of voucher specimen (voucher No. BD070701) are slow, sustained contraction of smooth muscle available in the herbarium of Research Center of cells through Ca2+ influx, as shown through the Tianjin Zhongxin Pharmaceuticals. experiments using phorbol esters and isozyme- Adult male and female New Zealand specific blockade (19, 20). Our previous study white rabbit (2.0-2.5 kg) were obtained from proved quite consistent with this (6). Laboratory Animal Center of Peking University The commonly used models of analgesia (Beijing, China). All animals were housed at the contain thermal stimulation, electrical Experimental Animal Center of Tianjin Medical stimulating method, mechanical irritation and University (Tianjin, China) and kept under chemical stimulus. With different models, there standard environmental conditions. Animals had can be differences in the analgesic effects of free access to water, but food was withdrawn 24 selected drugs; some trends can be identified h before the experiments. KM mice (18-22 g) (21-22). The writhing test is an experimental were housed in plastic cages, with food and tap model used for the screening of drugs with water available ad libitum, in the colony room. analgesic activity, based on the irritation caused The animals submitted to oral administration of after the intraperitoneal injection of 0.6% acetic the extract or drugs were fasted for 24 h. acid. This injection can produce the peritoneal Animals’ experiments were performed with inflammation characterized through the the approval of the Institutional Animals Care contraction of abdominal muscles accompanying and Use Committee of China, and institutional an extension of the forelimbs and elongation of guidelines for animal welfare and experimental the body. This writhing response is considered conduct were followed. to be a visceral inflammatory pain model, and in this way, this acid causes the release of algesic Reagents and chemicals mediators such as bradykinin, prostaglandins, HPLC-grade acetonitrile was from histamine and 5-hydroxytryptamine. Merck (Darmstadt, Germany). Acetylcholine Additionally, although this test was a nonspecific (Ach), Hexamethonium, Methoctramine, model (e.g. anticholinergic and antihistaminic and 4-Diphenylacetoxy-N-methylpiperiding and other agents show activity in this test), it is methiodide (4-DAMP) were purchased from widely used for analgesic screening and involves Sigma (St. Louis, MO, USA ) and Verapamil local peritoneal receptors (23). Hydrochloride Injection was obtained from So in the present study, we examined the Hefeng Co., Ltd. (Shanghai, China). Atropine antinociceptive effects of SCT in acetic acid- sulphate injection and Noradrenaline Bitartrate 612 Antinociceptive and Smooth Muscle Relaxant Activity Croton tiglium Table 1. Possible compounds from SCTp and SCTe by HPLC-ESI(+)/MSn. M+H]+ or] NO Compound Molecular formula +[Fragment ions of [M+H]+ or [M+Na [M+Na]+ m/z 1 Deoxyphorbol acetate methylbutanoate C27H38O7 475.1 265.1 ,293.0 ,277.0 ,311.0 ,355.3 2 Phorbol acetate methylbutenoate C27H36O8 489.2 265.1 ,293.0 ,311.2 ,389.3 ,429.3 3 Deoxyphorbol acetate methylbutenoate C27H36O7 473.0 265.1 ,293.1 ,311.2 ,391.0 4 Phorbol methylbutanoate isobutyrate C29H42O8 519.6 265.1 ,293.0 ,311.0 5 Phorbol decanoate acetate C32H48O8 583.3 265.1 ,269.0 ,293.1 ,311.1 ,501.8 6 Phorbol acetate butyrate C26H36O8 499.1 265.0 ,293.1 ,311.2 ,417.3 were supplied by Jinhui amino Co., Ltd. (Tianjin, blow on the head. After a laparotomy incision, a China). Other chemicals were of the highest portion of the jejunum was removed and placed grade available. in an oxygenated Tyrode’s solution (composition in mM: NaCl 136.9, CaCl2 1.8, KCl 2.7, MgCl2 Extraction of the seed of C. tiglium 1.1, NaHCO3 11.9, NaH2PO4 0.4, and glucose SCT (2 Kg) was extracted with methanol 5.6, pH = 7.4). Respective five segments of (10L × 3) under reflux for 3 h. The methanol jejunum 2 cm in length were mounted in a 10 mL extracts (SCTm) were combined and evaporated organ bath containing Tyrode’s solution that was under reduced pressure in a rotary evaporator bubbled with a 95% O2 and 5% CO2 gas mixture to give an oily residue (250 g), with a yield of and the temperature was held at 37°С (6). 12.5%. The residue was suspended in aqueous and extracted with petroleum ether, ethyl acetate Contractile activity of smooth muscle and normal butanol. The extracted solutions Each segment was allowed to equilibrate in the were respectively evaporated under reduced bath for 50 min to obtain a regular spontaneous pressure to give P.E. parts (SCTp) (167 g), activity. An initial load of 1 g was applied to each EtOAc parts (SCTe) (8 g), n-BuOH parts (44 g) of the tissue and was kept constantly throughout and H2O fraction (8 g). Croton oil was the same
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